EP0626362A1 - Verfahren zur Reinigung von Pentafluorethan - Google Patents

Verfahren zur Reinigung von Pentafluorethan Download PDF

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Publication number
EP0626362A1
EP0626362A1 EP94108091A EP94108091A EP0626362A1 EP 0626362 A1 EP0626362 A1 EP 0626362A1 EP 94108091 A EP94108091 A EP 94108091A EP 94108091 A EP94108091 A EP 94108091A EP 0626362 A1 EP0626362 A1 EP 0626362A1
Authority
EP
European Patent Office
Prior art keywords
cfc
hfc
extracting reagent
boiling point
extracting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP94108091A
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English (en)
French (fr)
Other versions
EP0626362B1 (de
Inventor
Atsuo C/O Showa Denko K.K. Nishimura
Reiji C/O Showa Denko K.K. Takahashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Resonac Holdings Corp
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Showa Denko KK
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Publication date
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Application filed by Showa Denko KK filed Critical Showa Denko KK
Publication of EP0626362A1 publication Critical patent/EP0626362A1/de
Application granted granted Critical
Publication of EP0626362B1 publication Critical patent/EP0626362B1/de
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C07C17/386—Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds

Definitions

  • the present invention relates to a purification process of pentafluoroethane, and more specifically to a purification process of pentafluoroethane by an extractive distillation method using an extracting reagent.
  • Monochlorodifluoromethane (hereinafter referred to as HCFC-22) which has hitherto been widely used as a refrigerant, etc., for an air conditioner, refrigerator, etc., becomes an object of the world-wide regulation as a material of destroying the ozone layer existing in the stratosphere, that is, as a regulated fluorinated hydrocarbon.
  • pentafluoroethane (hereinafter referred to as HFC-125) having the similar properties as HCFC-22 has been watched with interest as one of substitutes for HCFC-22.
  • CFC-125 Since HFC-125 is usually produced by reacting perchloroethane and hydrogen fluoride as raw materials, monochloropentanfluoroethane (hereinafter referred to as CFC-115) is frequently contained in the product as a by-product.
  • CFC-115 also is an object of the world-wide regulation as a controlled fluorinated hydrocarbon (CFC) and must be separated.
  • a distillation method is the most general method. According to the inventors' investigations, however, the relative volatility of a little amount of CFC-115 to HFC-125 is near 1, for example, the relative volatility is from 1.01 to 1.02, under the pressure of near 5 kg/cm2 G, and hence it is very difficult to separate HFC-125 from CFC-115 by a simple distillation method.
  • U.S. Patent 5,082,329 discloses a process of separating HFC-125 from a crude HFC-125 containing CFC-115 by carrying out an extractive distillation using a controlled CFC as an extracting reagent.
  • the extracting reagent is exemplified with 1,2-dichlorotetrafluoroethane, etc. and the extracting reagent itself is a controlled CFC.
  • An object of the present invention is, therefore, to provide a process of purifying HFC-125, without using such a controlled CFC as an extracting reagent, by extractive distillation of a crude HFC-125 to separate HFC-125 from by-product CFC-115.
  • the above-described extracting reagent increases or decreases the relative volatility of CFC-115 to HFC-125 to be apart from 1, whereby the separation of the components becomes possible.
  • the relative volatility is well known and is defined as a ratio of the equilibrium constants of the constituting components of a fluid mixture.
  • the constituting components are HFC-125 and CFC-115
  • the relative volatility of CFC-115 to HFC-125 is shown by the following formula (1).
  • the extracting reagent for practical use is required to have the following properties.
  • the standard boiling point of the extracting reagent is necessarily higher than the standard boiling points of HFC-125 and CFC-115 to some extent. Practically, it is preferred that the difference in boiling point between HFC-125 or CFC-115 and the extracting reagent is at least about 30°C, and more preferably about 40°C or more. Since the boiling points of HFC-125 and CFC-115 are -48.5°C and -38.7°C, respectively, the extracting reagent preferrably has a standard boiling point of at least -10°C.
  • the boiling point should not be too high so that a specific heating source is not needed and the temperature distribution in a distillation column for separation of the extracting reagent can be moderated.
  • the difference in boiling point between HFC-125 or CFC-115 to be separated and the extracting reagent is not more than about 140°C, and more preferably not more than 120°C.
  • the relative volativity of CFC-115 to HFC-125 can be reduced to below 1, and preferably below 0.6 or the relative volativity can be increased to more than 1, and preferably at least 1.7, whereby HFC-125 and CFC-115 are separated from each other by extractive distillation and HFC-125 can be obtained at a high purity.
  • extracting reagents particularly preferred are n-pentane and acetone.
  • the concentration of the extracting reagent increases, it is more advantageous to make the relative volativity apart from 1.
  • the concentration is generally 30% by weight or higher, and preferably in the range of from 50% by weight to 90% by weight.
  • the foregoing extracting reagents may be used singly or as a mixture thereof. In the case of using them as a mixrure, it is possible to use those reducing the relative volatility of CFC-115 to HFC-125 to below 1 in combination, or to use those increasing the relative volatility to more than 1 in combination. However, it is not preferred to use an extracting reagent of reducing the relative volatility to below 1 and an extracting reagent of increasing the relative volatility to more than 1 in combination.
  • HFC-125 having a purity of 99.93% (containing 0.07% of CFC-115) was obtained as the distillate.
  • the purification process of HFC-125 according to the present invention is an excellent process capable of easily removing CFC-115 from HFC-125, the separation of which has hitherto been difficult by conventional processes.
EP94108091A 1993-05-25 1994-05-25 Verfahren zur Reinigung von Pentafluorethan Expired - Lifetime EP0626362B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP122869/93 1993-05-25
JP12286993 1993-05-25

Publications (2)

Publication Number Publication Date
EP0626362A1 true EP0626362A1 (de) 1994-11-30
EP0626362B1 EP0626362B1 (de) 1996-06-19

Family

ID=14846650

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94108091A Expired - Lifetime EP0626362B1 (de) 1993-05-25 1994-05-25 Verfahren zur Reinigung von Pentafluorethan

Country Status (10)

Country Link
US (1) US6179967B1 (de)
EP (1) EP0626362B1 (de)
KR (1) KR100333422B1 (de)
CN (1) CN1045288C (de)
AU (1) AU684757B2 (de)
BR (1) BR9402038A (de)
CA (1) CA2124282C (de)
DE (1) DE69400257T2 (de)
ES (1) ES2091069T3 (de)
GR (1) GR3020852T3 (de)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995021148A1 (en) * 1994-02-07 1995-08-10 E.I. Du Pont De Nemours And Company Process for separating pentafluoroethane from a mixture comprising halogenated hydrocarbons and chloropentafluoroethane
WO1995021147A1 (en) * 1994-02-07 1995-08-10 E.I. Du Pont De Nemours And Company Process for separating pentafluoroethane from a mixture comprising halogenated hydrocarbons and chloropentafluoroethane
FR2716449A1 (fr) * 1994-02-24 1995-08-25 Atochem Elf Sa Procédé de purification du pentafluoroéthane.
WO1995024370A1 (en) * 1994-03-11 1995-09-14 E.I. Du Pont De Nemours And Company Separating and removing impurities from tetrafluoroethanes by using extractive distillation
WO1995027689A1 (en) * 1994-04-08 1995-10-19 Imperial Chemical Industries Plc Process for the purification of pentafluoroethane
WO1996006063A1 (en) * 1994-08-24 1996-02-29 Imperial Chemical Industries Plc Purification of pentafluoroethane
WO1996023752A1 (en) * 1995-02-01 1996-08-08 E.I. Du Pont De Nemours And Company SEPARATING AND REMOVING IMPURITIES FROM 1,1,1-TRIFLUOROETHANE (HFC-143a) BY USING EXTRACTIVE DISTILLATION
US5723429A (en) * 1994-03-11 1998-03-03 E. I. Du Pont De Nemours And Company Azeotropic or azeotrope-like compositions of tetrafluoroethane and chlorotetrafluoroethane
WO1999007660A1 (en) * 1997-08-12 1999-02-18 E.I. Du Pont De Nemours And Company Purification of difluoromethane by extractive distillation
US5990364A (en) * 1996-08-30 1999-11-23 Schirmann; Jean-Pierre Purification of pentafluoroethane
US6039845A (en) * 1997-01-06 2000-03-21 Elf Atochem S.A. Process for the purification of pentafluoroethane by extractive distillation
EP1153907A2 (de) * 2000-05-09 2001-11-14 Ausimont S.p.A. Verfahren zur Reinigung von Pentafluorethan (HFC-125)
EP1559702A1 (de) * 2004-01-30 2005-08-03 Solvay S.A. Verfahren zur Herstellung eines Hydrofluoralkans
US7060165B2 (en) * 2002-02-14 2006-06-13 Pcbu Services, Inc. Processes for purification and production of fluorocarbons
US20120215040A1 (en) * 2009-10-27 2012-08-23 Showa Denko K.K. Fluorine-containing compound purification method
US10370313B2 (en) 2016-02-26 2019-08-06 AGC Inc. Manufacturing method of purified 1-chloro-2,3,3,3-Tetrafluoropropene and purified 1-chloro-2,3,3,3-tetrafluoropropene (Z)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE191906T1 (de) * 1994-08-17 2000-05-15 Daikin Ind Ltd Verfahren zur herstellung von pentafluorethan
FR2730228B1 (fr) * 1995-02-07 1997-06-20 Atochem Elf Sa Procede de purification du pentafluoroethane
CN1120828C (zh) * 1999-11-10 2003-09-10 浙江省化工研究院 五氟乙烷的提纯方法
CN100999438B (zh) * 2007-01-04 2010-10-06 西安近代化学研究所 五氟乙烷的提纯方法
JP5477011B2 (ja) * 2009-02-03 2014-04-23 セントラル硝子株式会社 （ｚ）−１−クロロ−３，３，３−トリフルオロプロペンの精製方法
PT3239269T (pt) * 2014-09-25 2020-09-02 Daikin Ind Ltd Composição compreendendo hfc e hfo
JP6115550B2 (ja) 2014-11-17 2017-04-19 ダイキン工業株式会社 ＨＦＣ−２４５ｃｂと（Ｅ）−ＨＦＯ−１２３４ｚｅとを含有する組成物から両化合物を分離する方法
CN104557443B (zh) * 2014-12-03 2016-07-06 嵊州领航信息科技有限公司 一种制备五氟乙烷的系统和方法
CN114405041A (zh) * 2022-02-25 2022-04-29 明士新材料有限公司 一种用于电子级γ-丁内酯的精馏装置及其方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2442589A (en) * 1946-03-19 1948-06-01 Atomic Energy Commission Purification of perfluoroheptane by azeotropic distillation with methyl ethyl ketone
CH471760A (de) * 1966-02-23 1969-04-30 Ciba Geigy Verfahren zur Trennung von Gemischen von aliphatischen Fluorverbindungen
US5087329A (en) * 1991-05-16 1992-02-11 E. I. Du Pont De Nemours And Company Process for separating pentafluoroethane from a mixture of halogenated hydrocarbons containing chloropentafluoroethane

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL264123A (de) * 1960-04-28
NL131714C (de) * 1963-02-06
JP3182869B2 (ja) * 1992-05-18 2001-07-03 ダイキン工業株式会社 ペンタフルオロエタンとペンタフルオロクロロエタンとの共沸混合物およびペンタフルオロクロロエタンの分離方法
ES2096141T3 (es) * 1992-06-13 1997-03-01 Solvay Procedimiento para la eliminacion de impurezas olefinicas a partir de hidrocarburos c3-c6 fluorados.
US5346595A (en) * 1993-02-23 1994-09-13 Alliedsignal Inc. Process for the purification of a pentafluoroethane azeotrope

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2442589A (en) * 1946-03-19 1948-06-01 Atomic Energy Commission Purification of perfluoroheptane by azeotropic distillation with methyl ethyl ketone
CH471760A (de) * 1966-02-23 1969-04-30 Ciba Geigy Verfahren zur Trennung von Gemischen von aliphatischen Fluorverbindungen
US5087329A (en) * 1991-05-16 1992-02-11 E. I. Du Pont De Nemours And Company Process for separating pentafluoroethane from a mixture of halogenated hydrocarbons containing chloropentafluoroethane

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995021147A1 (en) * 1994-02-07 1995-08-10 E.I. Du Pont De Nemours And Company Process for separating pentafluoroethane from a mixture comprising halogenated hydrocarbons and chloropentafluoroethane
WO1995021148A1 (en) * 1994-02-07 1995-08-10 E.I. Du Pont De Nemours And Company Process for separating pentafluoroethane from a mixture comprising halogenated hydrocarbons and chloropentafluoroethane
FR2716449A1 (fr) * 1994-02-24 1995-08-25 Atochem Elf Sa Procédé de purification du pentafluoroéthane.
EP0669302A1 (de) * 1994-02-24 1995-08-30 Elf Atochem S.A. Verfahren zur Reinigung von Pentafluorethan
US5723429A (en) * 1994-03-11 1998-03-03 E. I. Du Pont De Nemours And Company Azeotropic or azeotrope-like compositions of tetrafluoroethane and chlorotetrafluoroethane
WO1995024370A1 (en) * 1994-03-11 1995-09-14 E.I. Du Pont De Nemours And Company Separating and removing impurities from tetrafluoroethanes by using extractive distillation
US5470442A (en) * 1994-03-11 1995-11-28 E. I. Du Pont De Nemours And Company Separating and removing impurities from tetrafluoroethanes by using extractive distillation
WO1995027689A1 (en) * 1994-04-08 1995-10-19 Imperial Chemical Industries Plc Process for the purification of pentafluoroethane
WO1996006063A1 (en) * 1994-08-24 1996-02-29 Imperial Chemical Industries Plc Purification of pentafluoroethane
US5830325A (en) * 1995-02-01 1998-11-03 E. I. Du Pont De Nemours And Company Separating and removing 1, 1, 1-trifluoroethane by using azeotropic distillation
WO1996023752A1 (en) * 1995-02-01 1996-08-08 E.I. Du Pont De Nemours And Company SEPARATING AND REMOVING IMPURITIES FROM 1,1,1-TRIFLUOROETHANE (HFC-143a) BY USING EXTRACTIVE DISTILLATION
US5990364A (en) * 1996-08-30 1999-11-23 Schirmann; Jean-Pierre Purification of pentafluoroethane
US6039845A (en) * 1997-01-06 2000-03-21 Elf Atochem S.A. Process for the purification of pentafluoroethane by extractive distillation
WO1999007660A1 (en) * 1997-08-12 1999-02-18 E.I. Du Pont De Nemours And Company Purification of difluoromethane by extractive distillation
EP1153907A2 (de) * 2000-05-09 2001-11-14 Ausimont S.p.A. Verfahren zur Reinigung von Pentafluorethan (HFC-125)
EP1153907A3 (de) * 2000-05-09 2002-07-17 Ausimont S.p.A. Verfahren zur Reinigung von Pentafluorethan (HFC-125)
US7060165B2 (en) * 2002-02-14 2006-06-13 Pcbu Services, Inc. Processes for purification and production of fluorocarbons
EP1559702A1 (de) * 2004-01-30 2005-08-03 Solvay S.A. Verfahren zur Herstellung eines Hydrofluoralkans
FR2865731A1 (fr) * 2004-01-30 2005-08-05 Solvay Procede de fabrication d'un hydrofluoroalcane
US20120215040A1 (en) * 2009-10-27 2012-08-23 Showa Denko K.K. Fluorine-containing compound purification method
US8692038B2 (en) * 2009-10-27 2014-04-08 Showa Denko K.K. Fluorine-containing compound purification method
US10370313B2 (en) 2016-02-26 2019-08-06 AGC Inc. Manufacturing method of purified 1-chloro-2,3,3,3-Tetrafluoropropene and purified 1-chloro-2,3,3,3-tetrafluoropropene (Z)

Also Published As

Publication number Publication date
CN1045288C (zh) 1999-09-29
DE69400257D1 (de) 1996-07-25
AU684757B2 (en) 1998-01-08
BR9402038A (pt) 1995-03-07
ES2091069T3 (es) 1996-10-16
CN1098710A (zh) 1995-02-15
US6179967B1 (en) 2001-01-30
KR100333422B1 (ko) 2003-03-04
AU6328394A (en) 1994-12-01
GR3020852T3 (en) 1996-11-30
CA2124282C (en) 2004-06-29
CA2124282A1 (en) 1994-11-26
EP0626362B1 (de) 1996-06-19
DE69400257T2 (de) 1997-02-13

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